First, let me say that I found playing the Silver Shroud to be a real hoot... So much tongue in cheek, so much nostalgia, so over-the-top hokey that it was fun...
I have a question though. this is the spoiler part if you haven't played as the silver Shroud.
I tried several times, and I either failed to accomplish both goals, or I got myself killed each time unless I followed the dialogue. I thought perhaps if I had a .50 or some equivelent I might have been able to pull it off... but with the weapon provided, it was just impossible for me at level 20.